Senior Ruby on Rails Engineer

Rockstar is recruiting for a venture-backed startup on a mission to simplify real estate law. Our client provides end-to-end real estate legal services through a proprietary digital platform and an experienced legal team, bringing clarity, transparency, and efficiency to property transactions in Canada. They are a team of dynamic professionals building a modern legal platform.

Hybrid (Toronto-based) |

Full-time |

Start date: ASAP

About the Company Our client is a venture-backed startup on a mission to simplify real estate law. They provide end-to-end real estate legal services through a proprietary digital platform and an experienced legal team, bringing clarity, transparency, and efficiency to property transactions in Canada.

✨ The Role We are hiring a Ruby on Rails Engineer with 2+ years of experience building production Ruby on Rails applications to join as an early engineering hire. The successful candidate will be expected to lead technical design for complex features and make sound architectural decisions in collaboration with the team.

They will build systems that power client-facing products, internal legal tools, and partner integrations. This is a rare opportunity to take real ownership and help shape both the product and engineering practices from the ground up.

What You’ll Work On

Designing, building, and maintaining production Ruby on Rails systems

Designing APIs, data models, and system architecture for complex workflows

Owning end-to-end feature development across client, internal, and partner tools

Refactoring and improving systems for scalability, performance, and reliability

Contributing to front-end features when needed (React)

✅ What You Bring to the Table

2+ years of professional experience building and maintaining production Ruby on Rails applications

Ability to independently scope, design, and deliver complex features with minimal oversight

Comfort working across the stack, with a backend focus

Strong fundamentals in Rails architecture, API design, and relational databases

Product-minded, collaborative, and comfortable with ambiguity

Nice to Have

Experience mentoring other engineers or contributing to engineering standards and best practices

Experience in startup or fast-paced product environments

Familiarity with React, Next.js, PostgreSQL, or GraphQL

Experience in regulated or complex domains

What Is Offered

Early team member at a venture-backed startup

Competitive salary + Employee Stock Option Plan (ESOP)

Full benefits package

3 weeks paid vacation, plus bank holidays and annual holiday shutdown

Hybrid model (3 days in downtown Toronto office + 2 days WFH)

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